high, it was originally built in 1929 as a
lab where student teachers could observe
children playing. Although it’s no longer
in official use, this overgrown dollhouse is
often open for tours during festivals.

Strolling past the quirky boutiques,
gardens and historic homes along German Street, I take a left on Mill Street,
and eventually reach the Rumsey Monument, which celebrates former resident
James Rumsey and his steamboat. The
tall stone column occupies a wonderful
perch on the bluffs above the Potomac.
From this viewpoint, the trains chugging
across the river on a long trestle bridge
look like pieces of a toy train set.

IF SHEPHERDSTOWN had an official verb, it might be “meander.” German Street, at the center of the compact
downtown, is an inviting place to wander in and out of shops. Popping in for
a drink at the funky Lost Dog Coffee,
I’m greeted by a unique taxidermy display featuring a squirrel holding a cell-phone and a pheasant being ridden by a
troll. The many varieties of biscotti here
are homemade.

German Street is also home to Four
Seasons Books, an independent bookstore with a maze of snug rooms, comfy
armchairs and used books upstairs.

Other stores are strong on housewares,Coffee & Candlery (where candles sharespace with regional wines and cheeses).

While any shopkeeper can recommend a good spot for lunch, the staff at
Pedal & Paddle can also tell you how to
work off those midday calories. The outfitter is a convenient spot to rent kayaks, canoes and bikes to use on the C&O
Canal and its towpath, located just outside town. If even thinking about exercising makes you feel like you deserve a
treat, try the lavender vanilla cupcakes
at the Shepherdstown Sweet Shop Bakery across the street.

A few blocks away on WashingtonStreet, O’Hurley’s General Store stocksan eclectic assortment of goods, fromold-fashioned toys to fair-trade mittensfrom South America, along with localhoney, cowbells, antiques, handmadechairs, birdhouses, decorative knobsand a few bins of hardware thrown intothe mix. Owner Jay O’Hurley was bornupstairs, back when his father ran thestore. Now he mans the front coun-ter next to an enormous woodstovethat keeps the building toasty on chillymornings. The great room at the backof the store is the place to be on Thurs-day nights, when O’Hurley’s hosts a jamsession of Appalachian and traditionalmusic in front of the fireplace.

Snatches of music drift through the
streets of Shepherdstown after dark, adding
to a surprisingly lively nightlife scene. It’s
not unusual to find someone strumming a
guitar or picking a banjo on a bench in front
of a coffee shop. Impromptu performances
aside, the Blue Moon Café, a popular restaurant, hosts live music on most weekend
nights. The intimate and historic Mecklenburg Inn has changed little since the late
1790s, and is now a pub with a large garden,
where I was allowed to cuddle the resident
orange cat, B.K. (for Bar Kitty).

Local organizations and Shepherd
University also host events ranging from
contra dancing to plays and free screenings of independent films. Another popular concert venue is the Opera House on
German Street, a former movie theater
that showed films from 1909 to 1956, and
today is mostly devoted to music.

With all this cultural activity, Shepherdstown may be a small town, but it’s
anything but sleepy. Even after 9 p.m.,
the streets are fairly full of people sipping coffee, chatting, heading to a pub or
leaving a concert.

The small-town spirit is still alive at
four-way stops, however, where the welcoming vibe of the place prevails. I keep
getting caught in a polite version of a
standoff that could be called a nice-off,
as other drivers take turns waving from
their cars and insisting that I go first.

After spending two days in Shepherdstown, I’m not surprised when I hear
Jim Ford, one of the innkeepers at the
Thomas Shepherd Inn Bed and Breakfast, say, “Many of our guests decided to
move to Shepherdstown after visiting for
the weekend.”

So come for the music, the hiking, the
history or the cupcakes. Just watch out
for that scary giant eye. n

Freelance writer and photographer Laurie
McClellan was so smitten with Shepherdstown that she checked its real estate listings as soon as she got home. To comment
on this story, email comments@bethesda
magazine.com.

The Bavarian Inn offers fine dining, with German
specialties such as spaetzle and wild game.